CEO Coaching: How Do I Refer My Boss to a Coach?

One statement I’ve heard too many times over the years is, “I wish my boss would talk to you/read your stuff/get a coach.” In truth, many organizations don’t foster honest conversations, nor do they use any type of 360-degree feedback process. So many senior executives breathe their own exhaust, believing they lead and manage effectively when they don’t. In fact, many are headed toward failure — they just don’t know it.

The further up you go in an organization, the less honest feedback you get. Many executives would welcome the opportunity to fix their bad or ineffective behavior, but they’re unaware. Although some are impervious to hearing criticism, many aren’t. Which one do you work for?

How do you approach your boss when they have some behavior or skill deficiency that holds back the team? Let’s explore a few options.

The direct approach. If you aren’t assertive, this is difficult. The direct approach requires someone adept at delivering tough messages (you) and someone mature enough to accept them (your boss). If you know that your boss has received tough messages from people whom they don’t have positional authority over, I encourage you to consider this. It sounds something like this: “Bob, can I share something with you that might be a bit difficult? (There’s a 99% chance he’ll say yes.) I’m not sure if you’re aware of this, but in our senior leadership meetings, people are afraid to disagree with you. As a result, I don’t think you get the benefit of good information that would help you with decisions. I say this because I want you and your team to be as successful as possible.” 

At that point, you’ll likely get a thank you (desired outcome) or rebuttal. If it’s a rebuttal, I’d follow up with, “My only desire is to help you.” Might there be retribution? Yes. Was it still the right thing to do? Yes. If the response is something along the lines of thank you (which may come immediately or sometime later), I’d merely say, “Let me know if I can help.” Alternatively, I have blogs about most CEO behavior and if you contact me, I can send you something that you can pass along.

I would not try this approach via email. It will cause him to wonder who else might have received a copy.

Indirect approach No. 1: Backchannel. If you have a strong human resources executive, or your boss has a peer whom you have a good relationship with, consider talking with them. Ask them if they’re willing to help or suggest a course of action. Once again, emphasize that you only want to help. If you have a reputation as a whiner (i.e., more interested in yourself than others), this won’t work (nor will any of these approaches). This method also has risk. It’s possible your boss finds out that you raised the issue and feels betrayed, so consider the maturity level of the peer or HR executive first.

Indirect approach No. 2: Change the process. In my work with CEOs and their teams, behavioral change often starts happening by changing the management process. If you can get a CEO to change the way they facilitate meetings and the team to agree upon rules of engagement, you have a fighting chance of getting people (including the CEO) to view their behavior differently. Consider saying to your boss, “It feels like you have a good perspective on where we need to take the business, but I don’t always feel like we’re aligned as a team. Have you ever considered bringing in someone to help you get all six cylinders firing at once to execute your vision?” Is this message a bit sycophantic? Yes. But if it allows an opening to work on the team and individual behaviors, you’ve won.

Indirect approach No. 3: The anonymous letter. If this doesn’t make you queasy, there’s something wrong with you. However, if you’re miserable, want to help the company and feel strongly that the other methods won’t work, why not anonymously alert your boss that they’re screwing up? Once again, only do this if you want to help and believe that, with awareness, your boss might change. This one also has risk and might blow up. I’m not talking about unethical or illegal behavior that causes you to think your boss needs coaching. That’s a legal event, not a coachable problem. I’m talking about poor leadership that can be resolved if you can get it into the light of day.

Indirect approach No. 4: “Thought you might enjoy this!” I’ve had clients come to me for coaching because one of their direct reports sent them some of my material on leadership, strategy or team effectiveness. The headline wasn’t, “Read this, you dope!” but rather, “I like the way this idea is presented and thought you might enjoy it.” 

Lastly, you should also identify what part of the problem you might play, or at least what you might do to help your boss succeed. There are no perfect bosses.

If your boss is a senior executive and you’re stuck on how to point out that their behavior or lack of knowledge or skill is causing problems, call me and we can discuss options.

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